


Demons and Angels

by Delta_Immortal



Category: Teen Wolf (TV)
Genre: 30s gangster!AU, Daddy Kink, Dirty Talk, Gags, Gun Kink, M/M, Restraints, Rough Sex, Verbal Humiliation, gang rivals
Language: English
Status: Completed
Published: 2014-12-02
Updated: 2014-12-02
Packaged: 2018-02-27 20:09:09
Rating: Explicit
Warnings: Major Character Death
Chapters: 1
Words: 4,214
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2704982
Author URL: https://archiveofourown.org/users/Delta_Immortal/pseuds/Delta_Immortal
Summary: <blockquote class="userstuff">
              <p>PWP 30s Gangster AU. </p><p>Derek lives in the lucrative world of sin. Something about rival gang member Stiles inspires him to look beyond that world, but it doesn't matter. It's not like Derek can go there anyway. So maybe he just settles on taking Stiles to heaven as often as he can.</p>
            </blockquote>





	Demons and Angels

**Author's Note:**

> Heed the warnings. One of our main characters (Derek or Stiles) dies at the end.

Life is short, so take what you can, his mother told him. You’ll never know how long it’ll last.

It’s true. It’s why he signs up for Peter’s jobs, joins the family business. Family’s all he’s got left now and he doesn’t know how long that will be. So he stays next to Peter for now, doing his dirty work and odd jobs. There’s money to be had in sin and you meet the most interesting people.

Like right now. Two men are coming in for a meeting; a rival gang, up the river from Beacon Hills. Their leader McCall wants to make sure there’s no trouble and they play nice. McCall is business and directness- something the Hales appreciate. He frisks McCall and takes the gun and knife and McCall walks into Peter’s office, telling Stiles to stay outside. His bodyguard gives a smug grin at Derek. 

Derek decides to frisk him, too. 

As his hands hit Stiles’s hips, they sway suggestively. For a moment Derek’s sure he’s imagined it in the dank florescent light but the hips jut forward and Stiles breathes, “Just like that, Daddy.” His gut goes tight and he looks in Stiles’s eyes, something challenging. Stiles means to make him unnerved. Two can play at that game. 

Derek slides his hands around Stiles’s ass, squeezing just a little as he finds a hidden gun, trailing it up around Stiles’s front, up against his neck and on his cheek. He plays it over Stiles’s mouth. “Open up, little gunsel,” he breathes and the way Stiles’s eyes widen in recognition, a fellow _invert_ \- it’s enough to tell Derek that Stiles is very interested. That, and how Stiles is now falaciating his own gun, tongue running over the tip, swallowing the barrel.

Jesus. The gun is loaded, too. 

“Such a horny little thing, you naughty boy,” Derek murmurs, transfixed as he pushes the gun in deeper. Stiles makes a moan, eyes keeping focused on Derek’s. “You open up for everyone who frisks you like that? Hungrily drop to your knees and give their guns a shining?” 

Something snaps between them. Stiles drops to his knees, hands fumbling with Derek’s belt, finding his cock and pulling it out. He sucks it down, hurriedly- there’s not much time left between Peter and McCall and Derek fucks his face roughly, gun pressed against Stiles’s head. 

They both know he won’t fire.

He comes down Stiles’s throat silently, his mouth open and eyes wide. Stiles looks up at him through long lashes and pulls off with a pop, smug grin back on his face as he tucks Derek back in his pants, taking back his gun. “This was fun, Daddy,” he breathes in Derek’s ear, bringing Derek’s hand to his own erection. 

Someone in the office is moving and the two scramble back to their positions, one on each side of the door. McCall comes out first, thanking Peter, saying goodbye to Derek, and asking Stiles to walk with him. Peter motions for Derek to give their weapons back and Derek does and if Stiles already has his gun no one needs to know. McCall and Stiles walk away, Stiles’s ass swaying just a little underneath his long trench coat.

Derek watches Stiles’s ass for a moment before turning to Peter. “Well?” 

Peter calls him back into the office where it is silent and safe. “They’ll be in town for a couple of days. They’re getting liquor from our brewery, want to check out the source and make sure it’s legit.” Peter shrugs. “Not a big deal.” He looks at Derek. “I need you to collect tonight,” he commands. Derek nods. 

 

***

 

Derek takes the gun, hidden in his suitcase, directly from Peter’s office to his car. There’s not much point in living anywhere else. Everyone fears this burnt-out husk of a mansion, a sign of Peter’s harsh and cruel wrath that not even his sister could escape. Derek doesn’t mind living under Peter; both know the other man would tear his throat out in a heartbeat if he had the chance. So Derek lives with his uncle and occasionally brings back loud boys to fuck into the night, and his uncle brings back women and encourages them to share Derek’s bed. It’s a game, really.

When Derek opens the garage door, he notes someone has been in his car. Maybe Peter planted something on him or maybe it’s a trap- Derek can’t be sure. He opens the door to the backseat anyway, his eyes adjusting to the light and see a pert little ass up in the air, the owner stuck in the floor. 

Derek smirks to himself, dropping the suitcase. “What a surprise,” he murmurs, his hands sliding along the ass. The ass shivers before the owner makes little thrusts at Derek.

“Couldn’t wait, Daddy,” Stiles says perkily and Derek gives the globes a hard squeeze, hard enough to leave bruises. Stiles lets out a sinful moan, high and needy, and it isn’t long before Derek is tearing the other man out of his clothes and jamming his fingers roughly into that hole.

“So tight,” Derek breathes, pressing Stiles’s head into the cold leather of his backseat while his other hand keeps fucking Stiles’s hole roughly. Occasionally he’ll hit that spot that makes Stiles gasp and squirm and tighten so beautifully around his fingers, but for the most part he stays clear of it, trying to aim for as much ache and burn as he can for tomorrow, so Stiles will remember for days what it feels like to be fucked by Derek Hale. “Surprised there, pretty little cumslut,” he teases, and Stiles shivers, ass clenching beautifully in silent encouragement.  “Thought you’d open yourself for all the men. But just me, huh? Couldn’t wait for me to find you, had to come into my car and wait for me here, too much of a whore for a bed?” Derek teases, his fingers giving Stiles a sharp jab into his prostate, and Stiles is openly panting now, sweat sliding down his back. 

Stiles attempts to speak, and Derek removes his hands. “Wasn’t-“ Stiles breathes, but he stops and turns around. Derek reaches down for Stiles’s briefs, holding them up. The way Stiles flushes even further, the way Stiles licks his lips and nods, giving Derek the go ahead. 

“You’ve got the skin of an angel,” Derek murmurs, pulling Stiles into his lap. “So white, so pure. Like it’s made from the cum you crave,” Derek adds and Stiles shuts his eyes, chest heaving. Derek wipes his lubed up hands on the boxers places them over his shoulder, his non-lubed hand playing inside Stiles’s mouth. Stiles licks his fingers, sucks on them, getting them wet and slobbery. 

Derek’s other hand is playing on Stiles’s chest, dancing and pulling on the hairs he feels there. It’s a head rush, knowing he’s clothed but Stiles is completely naked, knowing someone so brazen as to suck him in the hallway and as to wait for him in the car. “But I’m a demon, little gunsel,” he breathes into Stiles’s ear, and Stiles looks at him, his eyes still challenging despite the haziness of lust and arousal. “And I’m going to make you love being my bitch.” 

He stuffs Stiles’s mouth with Stiles’s briefs, makes him taste the lube that Derek finger-fucked into him. With a quick surge forward, he presses Stiles’s cheek against the seat again but this time he grabs Stiles’s hands, pulling off his own tie and tying up his bitch nice and good for their fuck. This way Stiles won’t damage his car, won’t push back, won’t do anything but take Derek’s thick cock as he fills his angel bitch nice and good. 

Stiles whimpers as Derek tells him such. Derek presses the head of his cock into Stiles, the pretty pink hole sucking him in, and Derek nearly howls at the sensation. “Feel so good, pretty bitch,” he breathes, falling over Stiles’s body and nibbling at Stiles’s ear. “Feels so good inside you, pretty bitch, gunna fill you with all of my cream, going to keep you milked for days.” 

It doesn’t make sense, really, and later Derek will be embarrassed by the words that came out of his mouth, but for now Stiles nods desperately, willing to agree to anything that will help take the edge off. 

He massages the bruises already forming on Stiles’s ass cheeks, hands sneaking up to Stiles’s hips before he plunges forward, body violently thrusting into the pliant man before him. Stiles nearly screams through the gag as his body shudders, tightens, gets _hotter_. Derek grins. 

“Like that, bitch? Daddy found that special spot inside of you, the one that lets you scream and tell all the other studs you’re taken.” He snaps his hips forward again and Stiles does scream this time, through the gag, and the sound is sweet, rapturous, and Derek would swear if Stiles wasn’t already a sinner than this would be the moment he’d fall. 

“Good boy,” Derek breathes, his voice low and husky, his voice rough from the strain of orgasm building. He’s close, but Stiles is closer with the way Derek is hammering against his prostate. Derek smirks, one hand reaching around to feel the leaking cock. “Jesus,” he murmurs, “gushing just like a woman. Made for cock, weren’t you?” he slams his cock in one more time, balls spanking against Stiles’s ass and Stiles comes, body taught and tight like a string. Derek’s hand moves up into that pretty patch of pelvic hair, holding Stiles upright as he fucks into that tight heat, coming inside that delicious body before him. 

Here in the car, in the garage, in Peter’s fucking burned out mansion, Derek swears he’s found heaven.

It takes him a moment to come back to earth. He looks down at Stiles’s splotchy red body, still for once and pliant, the fuck taking all the energy out of him. Good. Derek places light, chaste kisses along his back as he undoes the tie. “Good boy,” he repeats. 

Stiles grabs onto the seat for dear life, spitting out his briefs. He hides his face from Derek for a moment. 

Derek pulls out, cock soft and sloppy. He watches the come drip out of Stiles’s ass and feels pride. He checks his watch; he’ll have to leave now if he wants to make Peter’s job in time. Instead he trails a finger down Stiles’s thigh, scooping up the cum and pushing it back into Stiles’s ass. “Want me to clean you up?” he asks. 

Derek never liked Peter that much anyway.

The voice is rough with use and sarcastic. “Oh, would you _kindly_ ,” Stiles jokes. His words quickly moaned prayers of Derek’s name as Derek licks him clean. “Derek, Derek, _Derek_ ,” Stiles chants, his fingers clutching at the seat with their white-knuckled grip. “I can’t…”

Derek grins as he reaches in between Stiles’s legs. “Seems like you can,” Derek assures him. “You were made for this,” he adds, continuing to use his tongue to dip in and out of that used hole. Stiles lets out a sob, a beg, and Derek tsks at him. “Where was that smug little bitch from earlier?” he asks. “Or is it that you can’t stand the thought of losing my cream inside you?” 

The answer is some half-formed keen, a whimper, a request for Derek to let Stiles come.

Derek doesn’t let Stiles come until thirty more minutes have passed.

 

***

 

McCall and Stiles leave town soon after that, but Derek still manages to find business in their town. Sin is everywhere, really. There’s a small diner on the highway between their towns, and well, maybe Derek recognized the car in the parking lot. 

When Derek enters the diner, Stiles doesn’t even look at him. When Derek slides into the booth next to him, Stiles practically jumps a mile. He quickly recovers, face smug and eyes burning with lust, the same lust that drives Derek mad. 

“You miss me?” Stiles flirts with him as the waitress turns away, and Derek slides his foot out of his shoe and into Stiles’s crotch as an answer. Stiles rubs against it invitingly, eyes darkening. 

“Something about you, anyway,” Derek agrees. “But I’m here for business.” He steals one of Stiles’s fries, popping it in his mouth as his foot comes back to the floor, resting on his shoe. It’ll be a bitch to put it back on when he leaves, but worth it to feel the outline of Stiles’s cock against his heel.

Stiles ignores him, taking a long sip of his drink. He’s like a kid with his mouth around a straw; his mouth is puckered around it and he’s looking up at Derek through those eyelashes. They’re going to fuck behind the diner, Derek knows. He’s going to hold Stiles up while he fucks into him, leaves Stiles’s ass wet and sloppy, teeth clacking together as they give one last attempt to shut the other up. 

And when Derek orgasms first, his slicked back hair falling into his eyes, he watches Stiles squeeze his eyes shut as Derek strokes his cock, watches as Stiles falls over that beautiful edge where bliss exists, all of their passion stuck behind a shitty little dinner in the middle of nowhere.

 

***

 

It’s a couple of months before he sees Stiles again. This time Stiles is on his territory, leant out as back-up to Peter for a messy job. Peter needs a couple of men tracked down; Derek is all too willing. Stiles flirts with him in the car, as they go into the business. 

Later, Derek doesn’t remember what they said, only that Stiles is in the middle of flirting when a man jumps out of nowhere and pulls a gun on them. Derek shoots over Stiles’s ear and the man falls over dead, bullet right between his eyes. Stiles stays behind as Derek dispatches the other men, leaving them bleeding and dead on the ground. 

“Distracted,” Derek tells him. “Don’t do it again.” 

“I knew you’d have me covered,” Stiles teases.

But back in the hotel room, the smug boy falls away; Stiles looks shaken. He won’t look at Derek, won’t have much to do with him. Maybe he’s too tired, Derek thinks, but Derek presses his lips to Stiles’s neck, a mockery of passionate lovers. Stiles’s eyes fall shut and Derek continues to decorate his shoulders and neck with warm kisses, sometimes hungry and nipping, sometimes soft and sweet. Stiles falls asleep in his arms like that, and Derek doesn’t mind. 

 

***

 

The next time McCall visits Stiles frisks _him_ ; hands traveling all over Derek’s body, riskily flirting and touching Derek in front of their bosses. Peter seems amused; McCall looks horrified. They go into their office to “let the boys play” and Stiles’s lips are crashing onto Derek’s in the hallway. “I missed you,” Stiles breathes onto Derek’s mouth and it’s not quite a lie. It’s been less than a month but it still feels like too much damn time. 

“Got something for you,” Derek hums into Stiles’s skin, hands diving below Stiles’s belt, and Stiles gasps into his ear, their movements quick and hurried. Stiles’s hips jut forward, rocking his cock against Derek’s palm. He gasps again, throwing his head against the wall as Derek slides to his knees- they’ve never done this before. Nothing quite like this, and it makes Derek warm and tingly and aroused to think of how much it’s turning Stiles on. 

His lips nurse at the head, his tongue swirling at the precome along the slit. Stiles bites down on one of his fingers, cock jerking to life. Derek smiles and then opens his mouth, scraping his teeth down the length of Stiles’s shaft, reminding him that though he’s got his nose in Stiles’s pubes, he’s still dangerous and in charge. 

It’s so surprise that Stiles likes the edge. His hips fuck mindlessly, roughly into Derek’s mouth and Derek swallows it all; every thrust, every jerk, every violent slap of balls against his chin, but especially every drop. He sucks Stiles down, sucks until Stiles is oversensitive and whimpering and pulls up, tucking Stiles back into his pants gently. 

He smirks as he takes Stiles’s weapon, holding it out in front of the exhausted man. Eyes go wide for a moment before Stiles laughs at him, nothing smug at all in his grin.

Derek’s broken through, maybe. As much as you can in this business. “Won’t Peter be mad at you?” Stiles asks him. “I wasn’t very quiet.” 

It’s a dangerous world for men like them, Derek knows, but he shrugs. “Nobody here other than us four,” he lies; there are six guards hidden around the building. He winces, too- his voice is rough and he sounds hoarse, but the shiver that runs through Stiles’s body at the sound of it makes Derek hot. “It’s a world of sin, Stiles,” he adds. “What’s one more to the pile?” 

Stiles adjusts his coat and looks like he did in the motel that night, lost and far away, trapped in his own mind. Derek leaves him to his business. They stand in silence for forty-five minutes until McCall comes out.

When Stiles leaves, Derek realizes his room key is missing. 

 

***

 

Derek comes back to his room to find Stiles on the bed, already lubed up and waiting. “Missed you,” Stiles lies easily, his lithe and long body enthralling Derek closer. Derek happily sheds his clothes, noting Stiles has left all of his on a mess on the bed. Derek crawls over him, holding up Stiles’s legs and just slides right in. Stiles throws his head back and lets out a cry, his hands moving up to the pillow and then back down to Stiles’s sides as he tries to compose himself. 

“Daddy,” the little angel breathes, “I needed this, daddy. Missed your big cock inside me.” He reaches up-

Something falls onto the floor. 

Derek looks down, hoping to get it- but no. He recognizes the shape by how it reflects the lamplight. 

A police badge. From Stiles’s clothes. 

The world goes still; Derek knows Stiles isn’t a dirty cop.s

Stiles freezes underneath him, eyes terrified. Everything has changed. Derek holds all power. 

Derek breathes. Stiles stays stiff. Derek’s not on duty, he decides, and his cock is engulfed by Stiles’s hot, sweet ass, so he snaps his hips to continue, letting Stiles feel the brutal thrusts of their fucking. “Pretty little copper whore,” Derek breathes, hands tightening on the legs he’s holding up. “Bet you like taking dirty criminal cock, don’t you? Made to take our cum, let it dirty you up, leak out of you while you shine that pretty badge.” 

Stiles gasps, eyes clenched shut. His body’s tightening around Derek, his hands are tight in the sheets. “Wonder what the others would say about you,” Derek continues, still pounding into him. “Most cops, they’re dirty for money. But you take cock at the drop of the hat, dirty cocks. You’d spread your legs and mouth so wide and pretty, wouldn’t you, for all those dirty sinner cocks?” 

Stiles comes with a shout, comes _untouched_ , his orgasm so strong he hits his own chin, white ejaculate flying through the air. Derek feels sweat trickle down his back as he takes in the body pulsing around him; blissed out in white sheets, hidden in the darkness of this motel room. An angel, disguised as a devil. Or maybe one that wants to fall. 

He pulls out of Stiles, still hard- he’s going to mark him. “Gunna mark you, pretty copper,” Derek breathes, setting Stiles’s legs down and sitting on his hips. Stiles’s eyes are still closed tight, not looking, caught, and Derek _wants_ his prey. “Every time you wash yourself you’re gonna think of me, how hungrily your ass sucks me down, nice and tight and deep.” 

Stiles shudders, cock twitching just a little. Derek strokes his own cock quickly, already close to that edge. When he comes, he hits Stiles’s face, and in afterglow he bites down on Stiles’s neck, marking the copper, breaking their rules. He wants everyone to know that Stiles is his, that this little pretty cum-bucket of a cop-whore is his, that this undercover agent belongs to him. He _has_ Stiles, he knows it.

Stiles huffs in that cocky way, but his hands are trembling. “This was fun,” he says. His voice is flat. Everything is wrong. 

There’s no place for a cop and an enforcer, and they both know it.

“It was,” Derek agrees, rolling off Stiles to let him get up. Stiles sits up, pulls on his clothes. He only looks back once, at the door. Derek can’t help it; he has to know, now that he knows Stiles isn’t a demon like him. “The car?” he asks. The implication hangs heavy in the air.

“My first,” Stiles answers him honestly, something akin to affection in his voice. Derek closes his eyes, the new information sinking into his chest. When he opens them, Stiles is gone into the night, probably forever.

Life is shit, so take what you can, Derek’s mother told him. You’ll never know how long it’ll last.

Derek breathes into the pillow and wonders why everything he cares about never lasts. 

 

***

 

Stiles is a little jumpier than usual, and that’s before Peter reveals his gun and threatens to shoot Scott. Peter thinks they’re there to take over the factory.

Derek hasn’t squealed that McCall is there to _shut it down_. He’s not sure why.

Automatically Stiles grabs his gun and aims it at Peter, and Peter sighs about the dramatics. He gives a motion to Derek to pull his gun, but McCall interrupts before Derek can refuse to follow Peter’s command.

“We don’t have to do this,” McCall says, dropping his gun in what Derek thinks is a moronic gesture of good faith. McCall is the sort of person who gets _killed_. Or, Derek notes, seeing Stiles still wound up, gun still trained on Peter, who gets _others_ killed. 

McCall orders Stiles to put the gun down. It’s a terrible idea. It’s a suicidal idea. Even Stiles knows that putting the gun down means certain death, given how white he looks. Stiles is smart. He doesn’t trust Peter or Derek, and he shouldn’t. 

Yet he starts putting the gun down.

Peter rolls his eyes, a victorious sneer on his face. Derek knows exactly what will happen. He’s seen it happen a thousand times before; this time will be no different. So he makes his body move, goes to intercept his uncle’s bullet and he feels his body go numb. He’s done it; kept it away from Stiles. Immediately he sees his Uncle’s body drop; the sound of gunfire registers only seconds later. Derek falls to the floor and looks up at a serious Stiles, his eyes still cold and hard and calculated. The bright lights overhead make sort of a halo around him. 

Stiles’s body twists and moves as he dispatches all of Peter’s hidden guards; Scott has hunkered down and is somewhere Derek can’t see. Derek doesn’t really want to see Scott, either. He’s pleasantly warm, here, underneath Stiles’s body. He doesn’t have to strain his neck in order to watch Stiles work.

“Shit,” someone says, and the gunfire drops. Stiles has probably killed all of them. “He’s alive, Stiles, but… I’m going to call for a doctor.” 

Derek knows he’s a hopeless case. He didn’t feel the bullets, but the pain is in the background, a sensation he’s pushing from his mind right now. Scott runs off, probably so he doesn’t have to watch Derek die.

What an asshole, Derek thinks, leaving the two of them alone. Things aren’t fixed between them, and they won’t be. Stiles would be far more comfortable with Scott at his side.

Stiles doesn’t look at him, but he does look around, eyes searching for more men.

“There were six,” Derek informs Stiles, his breath suddenly not enough for his lungs. He takes a couple of bigger breaths, trying to widen his throat, open his mouth. 

“Got them all, then,” Stiles agrees. Derek is on the floor and Stiles is standing, looking away, and all Derek wants is for Stiles to look at him. But Stiles is an angel, and Derek is a sinner, a demon, and angels never look at demons, really. 

“Never liked my uncle anyway,” Derek says, one last attempt at speech. It isn’t what he wants to say. It isn’t what he needs to say, and he’s so stupid, wasting his last breath like this. What an idiot he is, choosing an officer over family. Letting a fuck burrow into his heart like this. What a fucking moron.

Derek regrets none of it. He can’t breathe, but he tries again. “P…pre-hey,” he slurs, not enough air to make a “t” sound. “Angel.” 

There’s no way to see Stiles’s face as Derek's world goes dark, but there’s something warm now on his head. He can hear someone calling his name from far away, almost like that first night in the car. It's a good memory to take with him as the darkness engulfs him.


End file.
